Abstract
Two diazabicyclo analogues of maraviroc, in which the azabicyclooctane moiety is replaced by diazabicyclooctane or diazabicyclononane, were synthesized and tested, through a viral neutralization assay, on a panel of six pseudoviruses. The diazabicyclooctane derivative maintained a significant infectivity reduction power, whereas the diazabicyclononane was less effective. Biological data were rationalized through a computational study that allowed the conformational preferences of the compounds to be determined and a correlation between the inhibitory activity, the bridge length of the bicycle, and the rotational barrier around dihedral angle τ7 to be hypothesized. A high-field NMR analysis supported the modeling results. © The Royal Society of Chemistry.
Original language | English |
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Pages (from-to) | 422-433 |
Number of pages | 12 |
Journal | MedChemComm |
Volume | 8 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2017 |